The Rich Somers Report 12 Tax Strategies Your CPA Doesn't Know About: Tulum Retreat 2025 | Karlton Dennis E412
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Oct 18, 2025 
In this insightful discussion, Karlton Dennis, an elite tax strategist and investor, reveals cutting-edge tax strategies not commonly known to CPAs. He dives into the secrets behind Apple and Google's low tax payments and explains how short-term rentals can be leveraged for significant tax benefits. Learn about paying your kids tax-free, the importance of asset protection using Wyoming LLCs, and how to maximize deductions through self-rentals and family payroll. This is a masterclass for anyone looking to think like the wealthy.
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Watch Out For Depreciation Recapture
- Depreciation recapture obligates you to repay tax benefits if you sell quickly after claiming big deductions.
- Holding certain vehicles five years avoids recapture penalties after accelerated deductions.
Use Spouse's Real Estate Status
- If one spouse is a real estate professional (e.g., holds a real estate license), spouses can qualify jointly to use rental depreciation against active income.
- Track qualifying real estate activities carefully to meet IRS definitions and offset active income.
Flip STR To LTR After Tax Benefit
- Buy and operate an STR for a short period, perform cost segregation, then convert to long‑term rental to keep depreciation benefits.
- Time closings and transient stays strategically to meet material participation and placement‑in‑service rules.
